<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2016-05-22 03:45:21 UTC</creation_date>
  <update_date>2026-08-19 02:23:24 UTC</update_date>
  <accession/>
  <common_name>Procainamide</common_name>
  <class>SmallMolecule</class>
  <description>Procainamide is an organic compound with the formula C13H21N3O and an average molecular weight of 235.33 g/mol. Procainamide belongs to the benzoic acids and derivatives, a subclass of benzene and substituted derivatives within the organic compounds. It is recorded as being found in or released from 30 different sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antiarrhythmic of class I and III. Other recorded sources include building and construction materials such as ceilings, household items like credit card holders, and various household cleaning and consumer products, including soap detergents, bleaching agents, perfumes within detergents and soaps, and other smoking requisites such as cigar cigarettes. It is also associated with food processing and cookware, specifically in the processing of meats and fish, the preparation of wort, food preservation, and molasses and the treatment of molasses. Furthermore, it is found in electrical and electronic equipment, including antennas, amplifiers, adjustable resistors, colour television systems, and conductors or conductive bodies characterised by the conductive materials, among 10 others.

The compound is administered through oral, intravenous, and intramuscular exposure routes. Procainamide interacts with three recorded protein targets, acting as an inhibitor or other modulator of the sodium channel protein type 5 subunit alpha (SCN5A), the voltage-gated inwardly rectifying potassium channel KCNH2, and DNA (cytosine-5)-methyltransferase 1 (DNMT1).</description>
  <categories/>
  <types>
    <type>Human Neurotoxin</type>
  </types>
  <synonyms/>
  <chemical_formula>C13H21N3O</chemical_formula>
  <average_molecular_weight>235.3253</average_molecular_weight>
  <monisotopic_moleculate_weight>235.168462309</monisotopic_moleculate_weight>
  <iupac_name>4-amino-N-[2-(diethylamino)ethyl]benzamide</iupac_name>
  <traditional_iupac>procainamide</traditional_iupac>
  <cas_registry_number>51-06-9</cas_registry_number>
  <smiles>CCN(CC)CCNC(=O)C1=CC=C(N)C=C1</smiles>
  <inchi>InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)</inchi>
  <inchikey>REQCZEXYDRLIBE-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Benzene and substituted derivatives</class>
    <sub_class>Benzoic acids and derivatives</sub_class>
    <direct_parent>Aminobenzamides</direct_parent>
    <alternate_parents>
      <alternative_parent>Amino acids and derivatives</alternative_parent>
      <alternative_parent>Aniline and substituted anilines</alternative_parent>
      <alternative_parent>Benzamides</alternative_parent>
      <alternative_parent>Benzoyl derivatives</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Primary amines</alternative_parent>
      <alternative_parent>Secondary carboxylic acid amides</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternate_parents>
    <substituents>
      <substituent>Amine</substituent>
      <substituent>Amino acid or derivatives</substituent>
      <substituent>Aminobenzamide</substituent>
      <substituent>Aniline or substituted anilines</substituent>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Benzamide</substituent>
      <substituent>Benzoyl</substituent>
      <substituent>Carboxamide group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Primary amine</substituent>
      <substituent>Secondary carboxylic acid amide</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
    </substituents>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <descriptors>
      <descriptor>benzamides</descriptor>
    </descriptors>
  </taxonomy>
  <status>Detected and Not Quantified</status>
  <origin/>
  <cellular_locations/>
  <biofluid_locations/>
  <tissue_locations/>
  <pathways>
    <pathway>
      <name>Procainamide (Antiarrhythmic) Action Pathway</name>
      <smpdb_id>SMP0000324</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Procainamide Action Pathway (New)</name>
      <smpdb_id>SMP0126265</smpdb_id>
      <kegg_map_id/>
    </pathway>
    <pathway>
      <name>Procainamide Drug Metabolism Action Pathway</name>
      <smpdb_id>SMP0143463</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <state/>
  <appearance/>
  <experimental_properties>
    <property>
      <kind>logp</kind>
      <value>0.95</value>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-1.89</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.02e+00 g/l</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.95</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>15.75</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>9.04</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>4-amino-N-[2-(diethylamino)ethyl]benzamide</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>235.3253</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>235.168462309</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>CCN(CC)CCNC(=O)C1=CC=C(N)C=C1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C13H21N3O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>REQCZEXYDRLIBE-UHFFFAOYSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>58.36</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>72.25</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>27.69</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>6</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <route_of_exposure/>
  <mechanism_of_toxicity/>
  <metabolism/>
  <toxicity/>
  <lethaldose/>
  <carcinogenicity/>
  <use_source/>
  <min_risk_level/>
  <health_effects>#&lt;HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72241073c0&gt;</health_effects>
  <symptoms/>
  <treatment/>
  <drugbank_id>DB01035</drugbank_id>
  <hmdb_id/>
  <pubchem_compound_id>4913</pubchem_compound_id>
  <chembl_id/>
  <chemspider_id>4744</chemspider_id>
  <kegg_id/>
  <uniprot_id/>
  <omim_id/>
  <chebi_id/>
  <biocyc_id/>
  <ctd_id/>
  <stitch_id/>
  <actor_id/>
  <pdb_id/>
  <wikipidia/>
  <general_references/>
  <targets>
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      <target_id>BE0000197</target_id>
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      <target_id>BE0000892</target_id>
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      <target_id>BE0000090</target_id>
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  </targets>
</compound>
